3-Chloropropanesulphonyl chloride → 3-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamide

HRID 1969507ノート

反応式

HRID 1969507 の反応式
Cl.[S:2]([N:12]1[C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:21]([C@@H:24]4[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25]4)=[N:22][N:23]=3)[C:15]=2[CH:14]=[CH:13]1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:30][CH2:31][CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:30][CH2:31][CH2:32][CH2:33][S:34]([NH:29][C@H:26]1[CH2:27][CH2:28][C@@H:24]([C:21]2[N:20]3[C:15]4[CH:14]=[CH:13][N:12]([S:2]([C:5]5[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=5)(=[O:4])=[O:3])[C:16]=4[N:17]=[CH:18][C:19]3=[N:23][N:22]=2)[CH2:25]1)(=[O:36])=[O:35]

参加物

5

反応物 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 69014326(1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride

生成物 1

HCID 679981583-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamide収率 91%

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of (1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride (0.05 g, 0.11 mmol, prepared using E from Preparation #B.1 and HCl) and TEA (0.03 mL, 0.21 mmol) in DCM (5 mL) at about 0° C. was added 3-chloropropane-1-sulfonyl chloride (0.02 g, 0.11 mmol) dropwise. The reaction mixture was stirred at about 0° C. for about 1.5 h. The reaction mixture was diluted with 5% aqueous citric acid (10 mL), and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamide (0.052 g, 91%) as a brown residue: LC/MS (Table 1, Method a) Rt=2.18 min; MS m/z: 537 (M+H)+.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-cd26e9e9294d4c33b0a386cabfbb2ee0
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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